Up to two-thirds of adolescent girls report painful periods but few seek medical care for their dysmenorrhea. Dysmenorrhea is associated with multiple physical and psychological symptoms, and the delayed evaluation and treatment of dysmenorrhea contributes to a poor quality of life and can result in lifelong health problems, including chronic pelvic pain and infertility. It is recommended that an assessment of patients' menstrual cycles be performed regularly, as identification of abnormally painful menstrual cycles may reveal potential health problems, including pelvic diseases such as endometriosis and adenomyosis. Visits to primary care providers offer an opportunity to assess and educate adolescents and their families on normal menstrual physiology. The purpose of this article is to review the evaluation and management of dysmenorrhea. [Pediatr Ann. 2020;49(4):e176-e182.].